All Questions
10
questions
-2
votes
2
answers
423
views
How much can we extend the Finkelstein reaction?
Finkelstein reaction explicitly entails the conversion of an alkyl chloride or alkyl bromide to alkyl iodide by treatment with sodium iodide in acetone.
$$\ce{R−X + NaI→[acetone] R−I + NaX↓ }\\
\ce{(X$...
- 89
3
votes
0
answers
58
views
Why do different products form when alkali halide reacts with zinc in polar protic and aprotic solvents?
Let's take an alkali halide such as $\ce{CH3CH2Cl}$ the two reactions in polar protic and aprotic solvents are as follows:
$$
\begin{align}
\ce{CH3CH2Cl &->[Zn, CH3OH] CH3CH3}\tag{R1} \\
\ce{...
- 1,409
5
votes
1
answer
2k
views
Why is fluoride the most nucleophilic halide in aprotic solvents? [duplicate]
I am confused on the topic of electronegative nucleophiles, and polar aprotic solvents.
From my understanding, the more electronegative a nucleophile is, the weaker of a nucleophile it will be, ...
1
vote
1
answer
1k
views
How do quaternary ammonium salts catalyse SN2 reactions?
I am asked to identify the "best catalyst" for the reaction:
$$\ce{CH3(CH2)8CH2Br->[\ce{KCN}][\text{benzene}]CH3(CH2)8CH2CN}$$
The options are (A) benzyl chloride (B) aniline (C) N,N,N-...
- 9,881
0
votes
1
answer
463
views
Redox reactions of halides in hexane
When we have two test tubes and we add:
In the first test tube: hexane, aqueous solution of $\ce{NaCl}$ and aqueous solution of $\ce{I2}$
In the second test tube: hexane, aqueous solution of $\ce{...
user40808
1
vote
1
answer
2k
views
Nucleophilic Substitution Reactions help
Which halogenoalkane reacts fastest with sodium hydroxide?
A. 1-iodobutane
B. 1-chlorobutane
C. 2-chloro-2-methylpropane
D. 2-iodo-2-methylpropane
Iodine has a larger radius, thus less ...
12
votes
1
answer
1k
views
Why isn't a polar protic solvent used in the Finkelstein reaction?
Usually, in a nucleophilic substitution reaction, a stronger nucleophile replaces a weaker nucleophile.
In any polar protic solvent, the order of nucleophilicity is $\ce{F-}<\ce{Cl-}<\ce{Br-}&...
- 1,891
3
votes
0
answers
84
views
Can the directionality of an SN2 reaction depend on solvent polarity?
Because of the effects of solvation, halide ions have differing nucleophilicity in protic solvents vs aprotic solvents, iodide being the best nucleophile in protic solvents and fluoride being best in ...
- 630
13
votes
1
answer
6k
views
Why does water favour nucleophilic substitution over elimination?
The two broad ways a halogen can leave a haloalkane are nucleophilic substitution and elimination reactions.
I was told that elimination reactions (that form a double bond as a $H^+$ is also removed) ...
- 909
50
votes
2
answers
6k
views
How does chloroform degrade nitrile gloves?
Many of us have experienced the failure of nitrile gloves when exposed to chloroform. What's going on at a mechanistic level when this occurs?
I would guess that the chloroform dissolves some of the ...
- 1,050